Electrophilic aromatic substitution with N-methoxy-N-acylnitrenium ions generated from N-chloro-N-methoxy amides: syntheses of nitrogen heterocyclic compounds bearing a N-methoxy amide group was written by Kawase, Masami;Kitamura, Takahiro;Kikugawa, Yasuo. And the article was included in Journal of Organic Chemistry in 1989.Computed Properties of C10H13BrO This article mentions the following:
N-Methoxy-N-acylnitrenium ions, generated by treatment of N-chloro-N-methoxy amides with Ag2CO3 in CF3CO2H, react with arenes to give N-aryl-N-methoxy amides in good yields. In the intramol. cyclization of N-chloro-N-methoxy-2-phenylacetamides, the mode of cyclization is highly dependent on the nature of ortho or para substituent groups. Nitrenium ions can primarily attack 3 positions (C-1, C-2, and C-6) of a Ph ring. Normally they attack C-6. On the other hand, when the ortho position is occupied with a substituent group, they attack both C-2 and C-6, in the former case followed by a 1,2-substituent migration, which was proved by a deuterium labeling experiment Thus, o-ClC6H4CH2CONClOMe gave 71% 4-chloro-1-methoxyoxindole (attack at C-6) and 9% 7-chloro-1-methoxyoxindole (attack at C-2 followed by migration). When an OMe group is substituted on the ortho or para position, attack is at C-1 due to the effect of the electron-releasing OMe group. The products are spiro dienone compounds E.g., p-MeOC6H4CH2CH2NHClOMe gave 83% spiro dienone I. A general discussion of the utility and mechanistic details of these reactions is presented. In the experiment, the researchers used many compounds, for example, 1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3Computed Properties of C10H13BrO).
1-(3-Bromopropyl)-4-methoxybenzene (cas: 57293-19-3) belongs to organobromine compounds. Organo bromine compounds are versatile compounds and are widely used in diverse fields. Organo bromine derivatives are used in the dye sector, as an indicator in analytical chemistry (Bromothymol blue is a popular indicator). The reactivity of organobromine compounds resembles but is intermediate between the reactivity of organochlorine and organoiodine compounds. For many applications, organobromides represent a compromise of reactivity and cost.Computed Properties of C10H13BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary